Total Synthesis of Echinopines A and B: Exploiting a Bioinspired Late-Stage Intramolecular Cyclopropanation

PA Peixoto, JA Richard, R Severin, DYK Chen

Index: Peixoto, Philippe A.; Richard, Jean-Alexandre; Severin, Rene; Chen, David Y.-K. Organic Letters, 2011 , vol. 13, # 21 p. 5724 - 5727

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Citation Number: 19

Abstract

Total synthesis of echinopine A and B have been accomplished, based on a strategy that involved two transition-metal-mediated ene-yne cycloisomerizations. A modified Pd- catalyzed enyne cycloisomerization/intramolecular Diels–Alder cascade rendered a more streamlined synthesis of tricyclic ketone 15, and a Ru-catalyzed ene-yne cycloisomerization/ cyclopropanation resembled the late-stage [5/7]→[3/5/5/7] ring-forming sequence in the ...